Sodium Carbonate → CID 145857661

HRID 2216010노트

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HRID 2216010 반응식
[F:1][C:2]([F:21])([F:20])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1)[OH:4].[C:22]([O:26][C:27](=[O:48])[NH:28][C:29]([C:31]1[S:32][C:33]([S:46][CH3:47])=[C:34]([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41](Br)[CH:40]=2)(=[O:38])=[O:37])[CH:35]=1)=[NH:30])([CH3:25])([CH3:24])[CH3:23].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CCO>[C:22]([O:26][C:27](=[O:48])[NH:28][C:29](=[NH:30])[C:31]1[S:32][C:33]([S:46][CH3:47])=[C:34]([S:36]([C:39]2[CH:44]=[C:43]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([CH:3]([OH:4])[C:2]([F:1])([F:20])[F:21])[CH:6]=3)[CH:42]=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:35]=1)([CH3:25])([CH3:23])[CH3:24]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 218861552,2,2-Trifluoro-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)ethanolHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

생성물 1

HCID 145857661CID 145857661

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

Following the same procedure in Example 1, step c, reaction of 2,2,2-trifluoro-1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanol (123 mg, 416 mmol, as prepared in Example 28, step b), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (100 mg, 0.2 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosphine)palladium(0) (59 mg, 0.05 mmol, Strem Chemicals Inc, Newburyport, Mass.), Na2CO3 (800 μL, 2M aqueous), and toluene/EtOH mixture (2:1, 2.4 mL) afforded 100 mg (85%) after purification (SiO2, flash elution: 30% EtOAc in hexanes) of the title compound as a white foam. 1H-NMR (CDCl3; 400 MHz) δ 8.20 (t, 1H, J=1.7 Hz), 7.94–7.99 (m, 2H), 7.77–7.81 (m, 1H), 7.67 (br s, 1H), 7.57 (m, 1H), 7.27–7.34 (m, 1H), 7.15–7.21 (m, 2H), 5.11 (q, 1H, J=6.8 Hz), 2.51 (s, 3H), 1.49 (s, 9H). 19F-NMR (CDCl3; 400 MHz) δ −78.51 (d, J=6.9 Hz). ESI-MS (m/z): Calcd. for C25H25F3N2O5S3: 586.7; found: 586.7.

후처리

  1. customafforded 100 mg (85%)
  2. customafter purification (SiO2, flash elution: 30% EtOAc in hexanes) of the title compound as a white foam

출처 및 근거

ORD 기록
ord-5575a6ce15ad4d88ad2b669c4dfbd644
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109354B2

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